Knowledge-Based Approaches to H-Bonding Patterns in Heterocycle-1-Carbohydrazoneamides

Abstract

We applied the knowledge-based approaches from the CSD-Materials to three novel heterocycle-1-carbohydrazonamides, for which molecular geometry was obtained by means of ab initio calculations, to predict the topological properties of their supramolecular motifs in the crystalline phase. Our survey suggested competition between nitrogen atoms of the heterocycle and carbohydrazonamide moieties to act as acceptors of H-bonding with the donor -NH2 group that can result in polymorphism based on various H-bonded motifs. The possibility of H-bonded polymorphism was proven for imidazole- and triazole-1-carbohydrazones with the ToposPro knowledge databases, which contain information on relations between local connectivity of molecules and topology of the whole H-bonded system. Experimental structures obtained with single crystal X-ray diffraction belong to the most abundant H-bonded motifs with proposed probabilities in the range 6–44%, thus giving evidence that the CSD-Materials and ToposPro knowledge databases can be combined to successfully predict H-bonded networks even for molecular families with a small number of representatives.

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

“…Indeed, co-crystals of paracetamol with diamino-or bis(4-pyridyl)-containing co-formers contain molecules of paracetamol connected by more likely amide/hydroxo or amide/amide pairs of interactions [193]. A good correlation between H-bonding charge analysis and H-bond propensities was also demonstrated for crizotinib [189], and heterocycle-1-carbohydrazoneamides [194].…”

“…Mugheirbi and Tajber analyzed the FIM hotspots around the itraconazole molecule to understand the molecular environment in the mesophase [260]. The itraconazole lacks any donors of strong H-donors but has a number of competing acceptors of H- This tool has been applied mainly for the analysis of strong hydrogen bonds [54,170,190,194,[248][249][250][251] in accord with the first test functional groups suggested within this tool, and the first paper published to describe it. Mutual disposition of hot spots can be used to find functional groups of the same molecule [245], co-formers [243,249,250], active sites in a binding pocket of a macromolecule [252], or surface inhibitors [170], which match a given pattern of interaction preferences.…”

“…While relations between connectivity of an organic molecule and resulting network and corresponding propensities of their appearance have already been published [315,317], this approach does not allow evaluating the most abundant molecular connectivity of insufficiently studied families of organic compounds. Recently, maps of electrostatic potential, the Full Interaction Maps, and the H-bonding Propensities were compared as the tools to overcome this problem for heterocycle-1-carbohydrazoneamides [194]. Knowledge-based approaches demonstrated competition between various nitrogen atoms to act as acceptors of H-bonding with the donor -NH 2 group and allowed evaluating local molecular connectivity.…”

Peculiarities of supramolecular organization of cyclic ketones with vinylacetylene fragments

“…Although C-HÁ Á ÁO hydrogen bonds are weak, we demonstrated previously (Voronova et al, 2016) that the Full Interaction Maps (FIMs) tool (Wood et al, 2013) implemented within the Mercury package (Macrae et al, 2008) can be applied to estimate likely C-HÁ Á ÁO hydrogen-bonded motifs for chalcones, polyenones and pentenynones. This result is of importance because previously the tool had been applied mainly for the analysis of strong hydrogen bonds (Mugheirbi & Tajber, 2015;George et al, 2015;Vologzhanina et al, 2016;Sandhu et al, 2018;Wojnarska et al, 2018;Xing et al, 2018). Thus, in this article, we have also applied FIMs to investigate C-HÁ Á ÁO and C-HÁ Á ÁBr hydrogen bonding in order to understand the effectiveness of a priori prediction of intermolecular interactions in this family.…”

Hydrogen-Bonding Interactions in Luminescent Quinoline-Triazoles with Dominant 1D Crystals

“…One fundamentally important tool to elucidate this relationship between molecular form and function in the solid state is single-crystal XRD [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. A great many organic molecules and metal complexes have been synthesized and structurally characterized by this technique [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 ]. The controlled growth of crystals and material assembly, however, is still a challenge because of this lack of correlation between intermolecular forces and bulk morphology.…”